2-Phenyl isopropyl and t-butyl trichloroacetimidates: Useful reagents for ester preparation of N-protected amino acids under neutral conditions

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1557-1560

  Thierry, Josiane ^a   Yue, Chongwei ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID;

ALKYLATION; ARTICLE; ESTERIFICATION;

EID: 0032546216     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10851-6     Document Type: Article

References (13)

1. 1. Kokotos, G.; Chiou, A. Synthesis 1997, 168-170.
2. 2. Iversen, T.; Bundle, D. R. J. Chem.Soc., Chem. Comm. 1981, 1240-1241.
3. 3. Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem.Soc., Perkin Trans. I 1985, 2247-2250.
4. 4. Yue, C.; Thierry, J.; Potier, P. Tetrahedron Lett. 1993, 34, 323-326.
5. 5. Amstrong, A.; Brackenridge, L; Jackson, R.F.W. and Kirk, J. Tetrahedon Lett. 1988, 29, 2483-2486.
6. 6. Nakajima, N; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139-4142.
7. 7. Widmer, U. Synthesis, 1987, 568-570.
8. 8. Schmidt, R. Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
9. 2/THF(4/1, v/v) was used to achieve dissolution of Z-Ser-OH, Fmoc-Ser-OH and Z-D-Trp-OH.
10. 10. A 1M solution of commercially available t-butyl trichloroacetimidate(Aldrich, Senn Chemicals, Lancaster, NovaBiochem) in cyclohexane was prepared and stored at -20°C for an extended period of time.
11. 11. Reaction mixtures were analyzed by RP-HPLC. % of each compound was calculated from the area of the corresponding peak of the chromatogram recorded at 270nm.
12. 12. Kinoshita, H.; Ishikawa, H. and Kotake, H. Bull. Chem. Soc. Japan, 1979, 52, 3111-3112.
13. 13. Chevallet, P.; Garrouste, P.; Malawska, B. and Martinez, J. Tetrahedron Lett., 1993, 34, 7409-7412.